Playing by the Rules of the Game

“What do you do when you stop winning?”

In this episode, Sean and Matt drop the highlight reel and talk candidly about what it actually feels like when a once high-flying brand stalls, hits flat revenue, or even starts shrinking.

They unpack why every business has a “natural size,” why top-line obsession is the laziest definition of winning, and how to think more clearly about margin compression, momentum, and your own financial security as a founder.

From redefining success beyond horsepower-style revenue numbers, to product, channel, and positioning pivots, to doing the brutal “Fog of War” cuts instead of slow bleeding out, this is a tactical, psychologically honest roadmap for operators trying to diagnose stalled growth and decide whether to push for the next level or intentionally right-size the business and finally take money off the table.

Chapters

00:00 – Cold open: what it feels like when winning stops

02:20 – Why this episode matters: growth stalls, failure, and the messy middle

04:06 – Defining “winning”: growth vs profit, lifestyle, and the natural size of a business

07:18 – Survival first: financial security, changing goals, and evolving definitions of success

12:51 – Diagnosing stalled growth: macro forces, misalignment, and internal blind spots

17:42 – Tactical vs strategic stalls: product, category limits, and being in the wrong vehicle

23:48 – Playing by the rules of the game: CAC, channels, and market realities

33:13 – Diversification as defense: why building on rented land is dangerous

39:00 – When winning tactics stop working: SEO hits, waves crashing, and preparing for stall-outs

44:00 – Operating paranoid: assuming stalls, diversifying early, and the tradeoff of leaving money on the table

50:00 – Changing the business: adding new product lines, multiple business units, and hedging inside your own brand

56:00 – Rented land warning: Facebook media, platform dependency, and why omnichannel is non-negotiable

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